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The swimmer

HOW long can you hold your breath?...

As Wittgenstein observed, thinking is like swimming underwater. We must struggle against our natural buoyancy to reach down to the depth of a problem. — Roy A. Sorensen Thought Experiments OUP 1998 p.109

What does it mean to 'go deep' in philosophy? and why is it so hard?
Somewhere — I think in his Autobiography — Bertrand Russell made a similar point, when he confessed that he was able to do 'real thinking' for only a few minutes in a day. The rest of the time, one is just shuffling words around like counters on a board.
One suspects that Wittgenstein never actually swam underwater, for real. Because actually it isn't that difficult. Certainly not a 'struggle'. Underwater swimming is a matter of technique. You do a jack knife on the surface, point your head down and kick, and you're on your way to the bottom of the swimming pool or lake. Flippers help if you're diving down more than a few feet, but they are not essential. Ditto for mask and snorkel.
When Russell talked about 'moving counters around' he was talking about technique. He had in mind academic philosophy as it existed in his time, but the very same applies today. As a philosophy graduate student you've learned all the logical 'moves'. You've become proficient at it. So proficient, in fact, that you are no longer thinking but merely calculating. Going through the motions.
Sit in on the average philosophy seminar and that's mostly what you will hear. It sounds difficult and profound only because you haven't mastered the relevant techniques, the vocabulary and the logic of this particular problem area.
The hard thing, the really hard thing, with swimming underwater is getting over your fear of suffocation — the fear that prevents you from going deeper, exploring the rocks down there while the increasing quantity carbon dioxide in your lungs is beginning to make your head dizzy and your diaphragm ache. And knowing all the while that the deeper you go, the longer it will take to get back to the surface.
That is what real philosophical thinking is like. You've gone down a little way, maybe feeling quite pleased with yourself. But you know, you can see, how much further you could go, if you made the effort.
Then the fear kicks in.
Not everyone is capable of overcoming that fear. The army doesn't try to make the cowards among its new recruits courageous. It weeds them out. They fail the test.
Sadly, the same does not apply to the student intake in the average university department of philosophy.